- Discovery of N-Substituted (2-Phenylcyclopropyl)methylamines as Functionally Selective Serotonin 2C Receptor Agonists for Potential Use as Antipsychotic Medications
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A series of N-substituted (2-phenylcyclopropyl)methylamines were designed and synthesized, with the aim of finding serotonin 2C (5-HT2C)-selective agonists with a preference for Gq signaling. A number of these compounds exhibit 5-HT2C selectivity with a preference for Gq-mediated signaling compared with β-arrestin recruitment. Furthermore, the N-methyl compound (+)-15a, which displayed an EC50 of 23 nM in the calcium flux assay while showing no β-arrestin recruitment activity, is the most functionally selective 5-HT2C agonist reported to date. The N-benzyl compound (+)-19, which showed an EC50 of 24 nM at the 5-HT2C receptor, is fully selective over the 5-HT2B receptor. In an amphetamine-induced hyperactivity model, compound (+)-19 showed significant antipsychotic-drug-like activity. These novel compounds shed light on the role of functional selectivity at the 5-HT2C receptor with respect to antipsychotic activity.
- Zhang, Guiping,Cheng, Jianjun,McCorvy, John D.,Lorello, Paul J.,Caldarone, Barbara J.,Roth, Bryan L.,Kozikowski, Alan P.
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- The synthesis of novel polycyclic heterocyclic ring systems. 2. Naphtho[2,1-b:4,3-g]bisbenzo[b]thiophene
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The novel polycyclic heterocyclic ring system, naphtho[2,1-b:4,3-g]bisbenzo[b]thiophene was synthesized from 5-[2-(2-bromo-3-thienyl)ethenyl]naphtho[2,1-b][1]benzothiophene. The assignment of its 1H and 13C nmr spectra was also accomplished by utilizing two-dimensional nmr methods.
- Sasaki, Kenji,Tokuda, Osamu,Hirota, Takashi,Luo, Jiann-Kuan,Castle, Raymond N.
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- Synthesis of Poly(3-substituted thiophene)s of Remarkably High Solubility in Hydrocarbon via Nickel-Catalyzed Deprotonative Cross-Coupling Polycondensation
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Polythiophenes bearing a siloxane moiety in a substituent at the 3-position are prepared by deprotonative polycondensation of 2-bromo-3-substituted-thiophene with a bulky magnesium amide chloromagnesium 2,2,6,6-tetramethylpiperidine-1-yl lithium chloride salt (TMPMgCl·LiCl) catalyzed by a nickel complex. Deprotonation takes place at 60 °C for 1 h to form the corresponding thiophene magnesium species, which is subjected to the polymerization by addition of 0.1-5 mol % NiCl2(PPh3)IPr (IPr: 1,3-bis(2,6-diisopropylphenyl)imidazole-2-yl). Polymerization proceeds in a highly regioregular manner, and the molecular weight of the thus-obtained polymer is controllable by the ratio of monomer feed/catalyst loading to indicate Mn of up to 280 000 with narrow molecular weight distribution. Chlorothiophenes are also found to induce polymerization in a deprotonative manner with TMPMgCl·LiCl or nBuLi (the Murahashi coupling polymerization). The obtained polymers bearing a siloxane moiety in the substituent is revealed to be dissolved in a hydrocarbon allowing formation of thin film from hexane.
- Fujita, Keisuke,Sumino, Yugo,Ide, Kenji,Tamba, Shunsuke,Shono, Keisuke,Shen, Jian,Nishino, Takashi,Mori, Atsunori,Yasuda, Takeshi
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- Regioregular poly(thiophene-3-alkanoic acid)s: Water soluble conducting polymers suitable for chromatic chemosensing in solution and solid state
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Regioregular polythiophenes with pendant carboxylic acid functionality, poly(thiophene-3-propionic acid) (PTPA, 3) and poly(thiophene-3-octanoic acid) (PTOA, 4), were prepared as water soluble conducting polymers and their chemosensory response was studied. Treatment with aqueous base generated intensely colored water soluble conducting polymer salts, with the color varying both as a function of counter ion size and length of the carboxyalkyl substituent. PTPA showed a different colorimetric response to each of the alkali earth metals whereas the longer chain PTOA was only sensitive to ions larger than Et4N+. Distinct color changes were also noted in studies of divalent cations known to selectively bind carboxylates, such as Zn2+, Mn2+, and Cd2+. Cast films of PTPA have been found to act as sensors to acid vapor (Δλmax of up to 132 nm). IR shows that the polymer self-assembles upon HCl vapor exposure, and that the process is completely reversible, leading to a good solid-state sensor for acids. This work demonstrates that regioregular polythiophenes containing acid side-chains have tremendous potential in the development of new sensors. The self-assembly and disassembly of regioregular poly(thiophene-3- alkanoic acid)s were driven by the analytes. The conformational changes resulted in clear visual color changes. These polymers show great potential in the development of sensors.
- Ewbank, Paul C.,Loewe, Robert S.,Zhai, Lei,Reddinger, Jerry,Sauvé, Geneviève,McCullough, Richard D.
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- Synthesis, Structure, and Dynamics of Chiral Eight-Membered Cyclic Molecules with Thienylene and Cyclopropylene Units Alternately Connected
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A rhodium(II)-catalyzed asymmetric cyclooligomerization of bifunctional monomers possessing triazolyl and vinyl groups at 2,3- and 3,4-positions on the thiophene ring is studied. Structurally interesting cyclic dimers in which thienylene and cyclopropylene units are alternately connected are obtained as the major components. The eight-membered rings in the center are non-planar and adopt a tub-shaped conformation. We also observe the phenomenon of racemization caused by a tub-to-tub ring-flipping, the activation energy of which is determined as 108 kJ mol?1 by electronic circular dichroism spectra measurement.
- Ishihara, Yumi,Miura, Tomoya,Moritani, Shunsuke,Murakami, Masahiro,Nagata, Yuuya,Nakamuro, Takayuki
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supporting information
(2022/01/22)
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- A study on regulating the conjugate position of NLO chromophores for reducing the dipole moment and enhancing the electro-optic activities of organic materials
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In order to improve the first-order hyperpolarizability (β) of the chromophore and transform it into a high macroscopic electro-optic activity, a series of novel second-order nonlinear optical chromophores with different push-pull electron groups introduced on the thiophene π-conjugate bridge for tuning the shape and dipole moment (μ) of chromophores were designed and synthesized. These chromophores are based on the same thiophene π-conjugated bridge, where the donor (N,N-diethylaniline) and acceptor (2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile or malononitrile) are linked to positions 2 and 3 of thiophene, respectively, affording a boomerang-like shape instead of a rod-like shape. Besides, an electron-poor group, Br (bromine atom), or an electron-rich group, DEA (N,N-diethylaniline), as an auxiliary acceptor or donor are linked to position 5 of thiophene. In addition, all chromophores showed good thermal stability as per the results from the DSC and TGA analysis. Through UV-vis analysis and DFT calculation, it has been concluded that chromophores with additional electron-rich groups as auxiliary donors display better intermolecular charge-transfer (ICT) absorption and lower HOMO-LUMO energy gaps (ΔE). Furthermore, the boomerang-like chromophore with the same push-pull structure shows a smaller dipole moment (μ) and β value than the traditional FTC. The poling results of guest-host EO polymers FTC/APC, FTC-H/APC, FTC-Br/APC and FTC-DEA/APC with the same number density afford r33 values of 17 pm V-1, 11 pm V-1, 10 pm V-1 and 25 pm V-1, respectively. Although the β value of FTC-DEA is smaller than that of FTC, the r33 value of FTC-DEA (25 pm V-1) is 47% greater than that of FTC (17 pm V-1) under the same number density. Hence, the above-mentioned results indicated that regulating the conjugate position of chromophores can efficiently decrease the dipole moment of the chromophores, weakening the dipole-dipole interactions and thereby enhancing the macroscopic electro-optical activity of poled polymers. These results indicate the potential application of these novel chromophores in electro-optical devices.
- Zhang, Hui,Tian, Yanxin,Bo, Shuhui,Xiao, Linghan,Ao, Yuhui,Zhang, Ji,Li, Ming
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p. 1380 - 1390
(2020/02/11)
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- Synthesis and thermal investigations of eleven-membered ring systems containing one of the heavier group 14 element atoms Si, Ge, and Sn
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Unique eleven-membered rings containing silicon, germanium, and tin were synthesized in good yields by the reactions of the corresponding 1,2-bis((2-bromothiophen-3-yl)methoxy)benzenes with (C6H5)2ECl2 where E = Sn, Ge, Si. The Sn and Ge congeners were crystallized, but the conformers that these rings crystallized in, were quite different. As confirmed by Density Functional Theory (DFT) calculations, (C28H22O2S2Sn) assumes a unique crystal structure that leaves more room around the tetrel atom as compared to the crystal structure of the corresponding Ge compound. In the latter, the central cavity is quite open, whereas in the former, one of the methylene groups can fold inwards. Another consequence is the influence on the planes of the aromatic rings flanking the heterocycle. In the Ge case, the benzene ring is folded away from the central cavity, whereas in the Sn case, it is almost parallel to the imaginary axis through the center of the ring. Thermal analysis investigations (TGA and DSC methods) of these eleven-membered rings suggested the loss of a phenyl group in the first decomposition step. The decomposition temperature decreased from the Si containing heterocycle to Ge and was lowest for the Sn containing heterocycle.
- Appiah, Clement,Eleya, Nadi,Gesing, Thorsten M.,Gogolin, Mathias,Lork, Enno,Staubitz, Anne,Stauch, Tim
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supporting information
(2020/01/31)
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- One-Pot Regiodirected Annulations for the Rapid Synthesis of ?-Extended Oligomers
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We demonstrate the broad applicability of the annulation protocol combining, in one pot, a direct arylation and cross aldol condensation for the straightforward synthesis at gram-scale of ?-extended thiophene-based scaffolds. The regiospecific direct arylation drives the subsequent cross-aldol condensation proceed under the same basic conditions, and the overall protocol has broad applicability in the synthesis of extended aromatics wherein the thiophene ring is annulated with furans, pyridines, indoles, benzothiophenes, and benzofurans. These scaffolds can be further elaborated into ?-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.
- Bianchi, Gabriele,Botta, Chiara,Calcagno, Giuseppe,Etkind, Samuel I.,Nitti, Andrea,Osw, Peshawa,Pasini, Dario,Po, Riccardo,Swager, Timothy M.
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supporting information
p. 3263 - 3267
(2020/04/21)
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- Fine-tuning the solid-state ordering and thermoelectric performance of regioregular P3HT analogues by sequential oxygen-substitution of carbon atoms along the alkyl side chains
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Conjugated polymers in thin films tend to orient their backbones with respect to substrates through self-assembly when processed from a solution. The molecular packing orientation and crystallinity of polymer crystals have been found to play a critical role in terms of their electrical performance. Taking advantage of the shorter bond length and the smaller rotation energy of the CH2-O bond than those of the CH2-CH2 bond in an alkyl chain, a side-chain engineering strategy is reported, which involves sequential oxygen-substitution of the carbon atoms from the γ position outwards along the hexyls in regioregular poly(3-hexylthiophene) (RR-P3HT). The subtle disparity between the CH2-O and CH2-CH2 bonds is found to enable fine tuning of the solid-state organization of the corresponding RR-P3HT analogues, namely poly(3-(2-propoxyethyl)thiophene) (P3POET), poly(3-(3-ethoxypropyl)thiophene) (P3EOPT) and poly(3-(4-methoxybutyl)thiophene) (P3MOBT). The evolution of film microstructures is observed when doping with FeCl3 in nitromethane at room temperature, and so is their thermoelectric performance. The highest power factor of 19 μW m-1 K-2 was observed for the doped P3POET film, which presents a dominant edge-on orientation with the strongest crystallinity and the closest π-π stacking. At the doping time corresponding to the optimized power factors (PFs) for each polymer, the doped P3POET film maintains both relatively high Seebeck coefficient (S) and electrical conductivity (σ) close to their maximum values, while the other polymers show either higher S and much lower σ (P3HT) or higher σ but much lower S (P3EOPT and P3MOBT). The square dependence of the PFs on S together with higher σ amplifies the power factor value of P3POET, which is almost 2 times those of the other polymers (11-13 μW m-1 K-2).
- Chen, Liangjun,Liu, Wei,Yan, Yonggao,Su, Xianli,Xiao, Shengqiang,Lu, Xinhui,Uher, Ctirad,Tang, Xinfeng
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p. 2333 - 2344
(2019/03/05)
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- A 2 - bromo - 3 - thiophene carboxylic acid intermediates of the synthesis method (by machine translation)
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The invention relates to 2 - bromo - 3 - thiophenecarboxylic acid synthesis method, comprises the following synthetic steps: 1): by 3 - methyl thiophene as raw materials, adding N - bromosuccinimide synthesis of 2 - bromo - 3 methyl thiophene; 2): by the 2 - bromo - 3 methyl thiophene to carbon tetrachloride as solvent, azobisisobutyronitrile as initiator with the N - bromosuccinimide synthesis of 2 - bromo - 3 - (bromomethyl) thiophene; 3): by the 2 - bromo - 3 - (bromomethyl) thiophene is 2 - iodo acyl benzoic acid oxidation to obtain 2 - bromo - 3 - thiophene formaldehyde; 4): by the 2 - bromo - 3 - thiophene formaldehyde sodium hydroxide aqueous solution as the solvent, is potassium permanganate oxidation to obtain 2 - bromo - 3 - thiophenecarboxylic acid. The invention has the advantages of: this invention uses the first to 2 of bit bromine substituted, then 3 of the oxidation of the synthetic route, mild reaction conditions, reactants are cheap and easily obtained, the yield is high. 2nd, greatly inhibit the double-bromo product, increasing the yield. (by machine translation)
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Paragraph 0025; 0030; 0031; 0032; 0033
(2017/08/28)
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- Synthetic Utility of Arylmethylsulfones: Annulative π-Extension of Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling Reactions
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A straightforward and general method for the synthesis of annulated thiophene, dibenzothiophene, and carbazoles analogues has been achieved involving alkylation of 2-bromo-1-(phenylsulfonylmethyl)arene/heteroarene with arylmethyl bromides/heteroarylmethyl bromides using t-BuOK as a base in DMF, followed by Pd(0)-mediated intramolecular Heck coupling in the presence of K2CO3 in DMF at 80-140 °C. The attractive feature of this protocol is that a wide variety of π-conjugated heterocycles could be readily accessed by an appropriate choice of arylmethylsulfones and benzylic bromides.
- Sankar, Elumalai,Raju, Potharaju,Karunakaran, Jayachandran,Mohanakrishnan, Arasambattu K.
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p. 13583 - 13593
(2017/12/26)
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- Conjugated Thiophene-Fused Isatin Dyes through Intramolecular Direct Arylation
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We report on the design, synthesis, and properties of innovative, planar, π-conjugated compounds in which a thiophene ring is fused with the skeleton of the naturally occurring dye isatin. The synthesis is achieved in high yields making use of an intramolecular direct arylation reaction as the key step, making the overall process potentially scalable. The synthetic sequence has been demonstrated also for an isatin bearing fluorine substituents on the aromatic ring. NMR and X-ray studies demonstrate the crosstalk occurring between the fused, coplanar, and conjugated moieties, making these novel dyes with a donor-acceptor character. Cyclic voltammetry and UV-vis studies confirm very interesting HOMO-LUMO levels and energy gaps for the new compounds.
- Nitti, Andrea,Signorile, Marco,Boiocchi, Massimo,Bianchi, Gabriele,Po, Riccardo,Pasini, Dario
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p. 11035 - 11042
(2016/11/29)
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- Effect of conjugated side groups on the photovoltaic performances of triphenylamine-based dyes sensitized solar cells
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Three novel organic dyes (LD1, LD2 and LD3) with conjugated side groups on the thiophene π-bridge are designed and synthesized for dye sensitized solar cells (DSSCs). The photophysical, electrochemical, and photovoltaic properties of the dyes have been successfully tuned by incorporating different conjugated side groups into the thiophene π-bridges moieties of dyes. Compared with the analogous dyes with non-conjugated side groups, the side group-conjugated dyes exhibited wider absorption spectra, higher molar extinction coefficients, and better photovoltaic performances. For the LD2-based DSSCs, the maximum power conversion efficiency (PCE) of 7.71% is obtained under AM 1.5 G irradiation (100 mW cm-2). The result demonstrates that high-performance DSSCs can be acquired by choosing suitable conjugated side groups into the π-bridges moieties of organic dyes.
- Long, Jun,Liu, Xunshan,Guo, Huan,Zhao, Bin,Tan, Songting
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p. 222 - 231
(2015/10/19)
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- Bithiophene with winding vine-shaped molecular asymmetry. Preparation, structural characterization, and enantioselective synthesis
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Preparation of 2,2-bithiophene derivatives bearing ?-alkenyl groups at the 3,3-positions and ring-closing metathesis reactions of the obtained compound were performed. The reaction of bithiophene bearing 3-butenyl substituents 1 with 5mol% Grubbs 1st generation catalyst underwent ring-closing metathesis (RCM) to afford the cyclized product 7 showing winding vine-shaped molecular asymmetry in up to 88% yield. Enantioselective RCM was also achieved by the use of chiral SchrockHoveyda molybdenum-alkylidene catalyst in up to 87% ee.
- Toyomori, Yuka,Tsuji, Satoru,Mitsuda, Shinobu,Okayama, Yoichi,Ashida, Shiomi,Mori, Atsunori,Kobayashi, Toru,Miyazaki, Yuji,Yaita, Tsuyoshi,Arae, Sachie,Takahashi, Tamotsu,Ogasawara, Masamichi
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p. 1480 - 1486
(2017/08/02)
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- Synthesis and properties of regioregular poly(3-substituted thiophene) bearing disiloxane moiety in the substituent. remarkably high solubility in hexane
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Regioregular poly(3-substituted thiophene) derivative bearing pentamethyldisiloxane moiety at the 3-substituent is prepared by nickel-catalyzed polymerization reactions with dehydrobrominative or debrominative generation of the organometallic monomer. The monomer precursors 2-bromo-3-(4- pentamethyldisiloxybutan-1-yl)thiophene (1a) and 2,5-dibromo- 3-(4-pentamethyldisiloxybutan-1-yl)thiophene (1b) are prepared from 3-methylthiophene with 45 steps in overall good yields. Treatment of 1a with TMPMgCl¢LiCl at room temperature for 3 h forms an organometallic monomer and following the addition of a nickel catalyst affords the corresponding polythiophene bearing a disiloxane moiety in the side chain. The reaction of 1b with Grignard reagent leads to the similar monomer and addition of a catalytic amount of [NiCl2(dppe)] also affords polythiophene in highly regioregular manners. The obtained polythiophene is found to be dissolved in a hydrocarbon such as hexane.
- Mori, Atsunori,Ide, Kenji,Tamba, Shunsuke,Tsuji, Satoru,Toyomori, Yuka,Yasuda, Takeshi
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supporting information
p. 640 - 642
(2014/05/20)
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- Design and synthesis of thiophene dihydroisoquinolines as novel BACE1 inhibitors
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Utilizing a structure based design approach, combined with extensive medicinal chemistry execution, highly selective, potent and novel BACE1 inhibitor 8 (BACE1 Alpha assay IC50 = 8 nM) was made from a weak μM potency hit in an extremely efficient way. The detailed SAR and general design approaches will be discussed.
- Xu, Ying-Zi,Yuan, Shendong,Bowers, Simeon,Hom, Roy K.,Chan, Wayman,Sham, Hing L.,Zhu, Yong L.,Beroza, Paul,Pan, Hu,Brecht, Eric,Yao, Nanhua,Lougheed, Julie,Yan, Jiangli,Tam, Danny,Ren, Zhao,Ruslim, Lany,Bova, Michael P.,Artis, Dean R.
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p. 3075 - 3080
(2013/06/26)
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- Self-assembly behaviour of conjugated terthiophene surfactants in water
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Conjugated self-assembled systems in water are of great interest because of their potential application in biocompatible supramolecular electronics, but so far their supramolecular chemistry remains almost unexplored. Here we present amphiphilic terthiophenes as a general self-assembling platform for the construction of conjugated aggregates, providing access to aggregates with different morphologies without changing the basic molecular design. We explored the design parameters of these amphiphilic terthiophenes in detail, leading to the selection and synthesis of in total 8 new amphiphilic oligothiophenes. Their aggregation behaviour was investigated by absorbance and fluorescence spectroscopy, dynamic light scattering, and cryo-transmission electron microscopy. Critical micelle concentrations as low as 0.01 mM were found and different sized aggregates ranging from several nanometres up to 200 nm. The aggregate morphology could also be tuned by changing the substitution pattern of hydrophilic and hydrophobic moieties, leading to different types of aggregates ranging from globular- and elongated micelles to bilayers. Remarkably, aggregation had only little effect on the electronic and spectroscopic properties of the oligothiophenes, which will be of interest for their application in supramolecular electronics.
- Van Rijn, Patrick,Janeliunas, Dainius,Brizard, Aurelie M.,Stuart, Marc C. A.,Koper, Ger J. M.,Eelkema, Rienk,Van Esch, Jan H.
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scheme or table
p. 558 - 567
(2011/06/20)
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- Novel crown-containing 3-styryl derivatives of oligothiophenes: Synthesis, structure, and optical and electrochemical characteristics
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A method for the synthesis of the 3-substituted polythiophene derivatives including two crown-containing styryl fragments was proposed. The optical properties of the obtained compounds are characterized by the presence of intense absorption and fluorescence bands. The oxidation to the thiophene derivatives involves the crown-containing styryl fragment and should be sensitive to the presence of the metal cation in the crown ether cavity.
- Lukovskaya,Bobyleva,Fedorova,Fedorov,Anisimov,Didane,Brisset,Fages
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experimental part
p. 1509 - 1515
(2011/01/08)
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- Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents
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When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (e.g., ethoxycarbonylmethyltriphenylphosphonium bromide and n- butyltriphenylphosphonium bromide) form a ylid (when an α-carbonyl group is present) or lose a phenyl group to form alkyldiphenylphosphine oxides when treated with the base. Mechanistic investigation of the homocoupling reaction indicates that the reaction proceeds through a ylid that acts as a nucleophile on an unreacted phosphonium salt. The resulting adduct undergoes elimination to form the observed product. The EIZ ratio seems to depend on the amount of the base used and the phosphonium salt involved.
- Ngwendson, Julius N.,Schultze, Cassandra M.,Bollinger, Jordan W.,Banerjee, Anamitro
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p. 668 - 675
(2008/09/21)
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- Design, synthesis, and biological evaluation of the N-diarylalkenyl- piperidinecarboxylic acid derivatives as GABA uptake inhibitors (I)
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Twenty novel N-diarylalkenyl-piperidinecarboxylic acid derivatives were synthesized and evaluated as γ-aminobutyric acid uptake inhibitors. The biological assay showed that (R)-1-[4,4-bis(3-phenoxymethyl-2-thienyl)-3- butenyl]-3-piperidinecarboxylic hydro
- Zheng, Jianbin,Wen, Ren,Luo, Xiaomin,Lin, Guoqiang,Zhang, Jiange,Xu, Linfeng,Guo, Lihe,Jiang, Hualiang
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p. 225 - 227
(2007/10/03)
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- A convenient synthesis of symmetric 1,2-diarylethenes from arylmethyl phosphonium salts
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Symmetric ethenyldithiophenes are important intermediates for synthesis of photochromic materials and organic conductors. When acetonitrile is used as a solvent, 3-methylthiophenylphosphonium salts form symmetric ethenyldithiophenes in the presence of a strong base (e.g., NaH, tBuOK) in moderate to high yields. This homocoupling reaction is faster than a Wittig reaction with aromatic ketones in acetonitrile. Our study shows that the presence of polar aprotic solvents promotes the homocoupling reaction.
- Ngwendson, Julius N.,Atemnkeng, Walters N.,Schultze, Cassandra M.,Banerjee, Anamitro
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p. 4085 - 4088
(2007/10/03)
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- Heteroaryl radicals: A furyl radical in the synthesis of the tricyclic framework of eremophilane sesquiterpenoids
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Studies on the intramolecular addition of thieno and furan radicals to alkenyl groups are reported. The radicals undergo a 6-endo-trig selective cyclization to alkenyl systems resulting in a linearly annulated tricyclic moiety. Georg Thieme Verlag Stuttga
- Mal, Sajal K.,Some, Surajit,Ray, Jayanta K.
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p. 1951 - 1953
(2007/10/03)
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- Cyclic organoselenium compounds, their preparation and their uses
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The invention is directed to novel cyclic organoselenium compounds useful as antioxidants, pharmaceutical compositions containing them, and methods for their preparation.
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- Phosphorylamides, their preparation and use
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A phosphorylamide derivative represented by the general formula (I): STR1 wherein R represents an amino group that may be substituted, or a salt thereof, possesses potent antibacterial activity against Helicobacter bacterium, especially Helicobacter pylori, and is useful for prevention or treatment of digestive diseases caused by Helicobacter bacterium, solely or in combination with an antacid or an acid secretion inhibitor.
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- Search for surrogates: A study of endothelin receptor antagonist structure activity relationships
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The aryloxymethylene group was used as a replacement for an ester or amide bond present in a series of ET(A) selective endothelin antagonists. The effect of such replacement on the binding affinity is described.
- Raju,Okun, Ilya,Stavros, Fiona,Chan, Ming Fai
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p. 933 - 938
(2007/10/03)
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- An Efficient General Route to Furo-, Pyrido- and Thieno-benzazepines via Pd0 Catalysed Cross Coupling Reactions and Nitrile Ylide Cyclisations
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The cyclisation of diene-conjugated nitrile ylides of the general type 1, in which the conjugated system consists of a benzene ring and a five- or a six-membered heterocyclic ring, provides an effective route to fully unsaturated heterocyclobenzazepines.The combination of this cyclisation with a direct route to the nitrile ylide precursors via Pd0 catalysed cross-coupling gives an efficient general synthetic route to these systems from readily available starting materials.
- Finch, Harry,Reece, Donald H.,Sharp, John T.
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p. 1193 - 1204
(2007/10/02)
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- Selective oxabicycloalkanes
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A group of oxabicycloalkane herbicides of the formula, , JOCH2Q, , wherein J is a substituted oxabicycloalkane moiety; and, Q is optionally substituted phenyl or substituted thienyl;, exhibit selective herbicidal activity, especially in paddy rice. The compounds may be made e.g. by coupling an appropriately substituted thenyl bromide with the appropriate substituted oxabicycloalkanol.
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- Electrophilic Aromatic Substitution. Part 34. Partial Rate Factors for Detritiation of Dithienobenzene, Dithienobenzene, and Dithienobenzene
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Dithienobenzene (I), dithienobenzene (II), and dithienobenzene (III), specifically labelled with tritium in each position, have been synthesized.Their rates of protio-detritiation, in either anhydrous trifluoroacetic acid or mixtures of acetic acid and trifluoroacetic acid, have been measured at 70 deg C.The rate-acidity profiles for each compound show that there is weak hydrogen bonding between sulphur and trifluoroacetic acid, and the extent of this is closely similar to that previously found for thienothiophens thereby confirming the general trend observed with sulphur-containing heterocycles viz. that the extent of hydrogen bonding is proportional to the number of sulphur atoms in the aromatic compounds.Partial rate factors for detritiation, free from the effects of hydrogen bonding, are calculated as follows (position and compound in parentheses): 3.42E6 (1)-(I), 1.65E7 (2)-(I), 5.35E5 (4)-(I), 1.525E7 (2)-(II), 4.98E6 (3)-(II), 1.32E6 (4)-(II), 4.59E5 (5)-(II), 2.35E7 (7)-(II), 4.01E6 (8)-(II), 1.96E7 (2)-(III), 3.77E6 (3)-(III), 3.99E5 (4)-(III); the corresponding ?+ values are -0.745, -0.825, -0.655, -0.82, -0.765, -0.70, -0.645, -0.84, -0.755, -0.835, -0.75, and -0.64.The positional reactivity orders both within a given molecule and between molecules are satisfactorily predicted by localization energies calculated by the simple Hueckel method using the parameters αS 1.0, βCS 0.6, these having been found previously to predict correctly the positional reactivities in other sulphur-containing heterocycles.
- Archer, William J.,Cook, Robert,Taylor, Roger
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p. 813 - 820
(2007/10/02)
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